JPH03220176A - Insecticidal trifluoroacetyl derivative - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (Z is 2-chloro-5-thiazolyl or 2- chloro-5-pyridyl; R<1> and R<2> are H or methyl; R<3> is amino, methylamino or dimethylamino; Y is CH, N or of formula II). EXAMPLE:1-(2-Chloro-5-pyridylmethylamino)-1-methylamino-2- trifluoroacetylethylene. USE:An insecticide. PREPARATION:The objective compound can be obtained by reaction between a compound of formula III (Ya is Y=CH or N) and a compound R<3>-H.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to trifluoroacetyl derivatives, their preparation and use as insecticides.

DE-A 3639877 (West German Published Patent Application), which was known before the filing date of the present application, describes heteroarylalkyl-substituted 5- or 6-membered heterocycles having insecticidal and acaricidal activity. Further, EP-302389 (European Patent Publication) describes α-unsaturated amines having insecticidal and acaricidal activity.

The present inventors have now discovered a trifluoroacetyl derivative of the following formula (r).

Formula: In the formula, Z represents a 2-chloro-5-thiazolyl group or a 2-chloro-5-pyridyl group, and RI and R2 are each
represents a hydrogen atom or a methyl group; R″ represents an amino group, a methylamino group, or a dimethylamino group; and the compound of the present invention can be synthesized, for example, by the following method.

Formula: In the formula, Z, R', R'' and Ya are the same as above, and the formula: %Formula%() In the formula, R3 is the compound represented by the same as above to react. The compound represented by the formula (I a) is reacted with a compound represented by the formula: % formula %, in which Z, R' and R2 are the same as above. A method for producing a compound.

A method for producing a compound represented by the following formula, wherein Z, R', R2, R3 and Ya are the same as above.

Production method b) (When Y is represented by Ya) Formula: In the formula, Z, R', R'' and R3 are the same as above, characterized in that the compound is reacted with trifluoroacetic anhydride A method for producing a compound represented by the formula: wherein R3 and Ya are the same as above, 0-tox CCFs, where Z, R', Rz and R3 are the same as above.

The trifluoroacetyl derivative of formula (I) of the present invention exhibits a strong insecticidal action.

According to the present invention, although a part of the trifluoroacetyl derivative of formula (1) is conceptually included in EP-302389, there are no specific compounds disclosed in the present invention in the application specification. However, the formula (1) of the present invention is a new compound that has not been described in any publications known before the application.

Surprisingly, the trifluoroacetyl derivative of formula (1) of the present invention, for example, the above-mentioned EP-
Compared to the compounds specifically disclosed in No. 302389 and other general concept compounds other than the compounds of the present invention, it exhibits substantially excellent insecticidal activity.

In the compound of formula (1) of the present invention, preferably Z is 2
-chloro-5-pyridyl group, R1 represents a hydrogen atom, Rt represents a hydrogen atom or a methyl group, R3 represents a methylamino group, and 7 represents the formula (I) of the present invention. Specific examples of the compound include the following compounds.

1-(2-chloro-5-pyridylmethylamino)1-methylamino-2-trifluoroacetylethylene, 1-methylamino-1-(N-methyl-N(2-chloro-5-pyridylmethyl)amine) 2-trifluoroacetylene, 1-(2-chloro-5-pyridylmethylamine) -methylamino-2-trifluoroacetylguanidine and 1-(2-chloro-5-pyridylmethylamino)1-methylamino-2, 2-bis(trifluoroacetyl)ethylene.

In production method a), the raw material is, for example, 1(2-chloro-5-pyridylmethylamino)-1methylthio-2-
When trifluoroacetylethylene and methylamine are used, the reaction formula is shown below.

In production method C), as a raw material, for example, 1-(2-chloro-5-pyridylmethylamino)-1methylamino-
When 2-trifluoroacetylethylene and trifluoroacetic anhydride are used, the reaction is expressed by the following reaction formula.

In production method b), as a raw material, for example, 2-chloro-
When 5-aminomethylpyridine and 1-methylamino-1-methylthio-2-trifluoroacetylethylene are used, the reaction is expressed by the following reaction formula.

In the above production method a), the compound of formula (n) as a raw material means a compound based on the definitions of ZSR', R'' and Ya above.

In formula (n), Z, R' and R2 are preferably
Synonymous with the preferred definitions given above. Y is preferably C
Indicates H or N.

The compound of formula (U) can be obtained by reacting a compound represented by formula (V1) below with a compound represented by formula (V).

The compound of formula (V1) includes some of the known compounds described in JP-A-63-150275, and can be obtained by the method described in the patent publication.

When Ya represents N in the compound of formula (V1), formula (■) is a new compound, for example, 2.2.2-trifluoroacetamide in the presence of a strong base, such as potassium hydroxide, It is obtained by reacting carbon disulfide with a methylating agent such as dimethyl sulfate.

, the compound of formula (V), which is the raw material for production method b) and is also the raw material when producing the compound of formula (If), is
It means what is based on the definitions of R' and Rt, and preferably has the same meaning as the preferred definitions above.

The compound represented by formula (V) is disclosed in U.S. Patent No. 4.499,
No. 097 and Nippon Kagaku Zasshi Vol. 83, pp. 218-222,
It is a known compound described in 1962, etc., and a representative example thereof is 5-aminomethyl-2-chloropyridine.

In production method b), the compound of formula (IV) as a raw material is
3 and Ya, and preferably has the same meaning as the preferred definition above.

The compound of formula (rV) can be obtained by reacting the compound represented by formula (Vf) with the compound represented by formula (V).

In production method C), the compound of formula (Ib) as a raw material means a compound based on the above definitions of Z, R1, R'' and R3, and preferably has the same meaning as the above preferred definition.

The compound of formula (Ib) can be obtained by production method a) and production method b).

When carrying out the above manufacturing method a), as a suitable diluent,
Mention may be made of all inert solvents.

Examples of such diluents include water; aliphatic, cycloaliphatic and aromatic hydrocarbons (optionally chlorinated) such as hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene. , methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, 1,2-dichloroethane, chlorobenzene,
Dichlorobenzene; Other ethers such as diethyl ether, methyl ethyl ether, di-iso-propyl ether, dibutyl ether, propylene oxide, dioxane, tetrahydrofuran; Ketones such as acetone, methyl ethyl ketone, methyl-1so-propyl ketone, methyl-1so -butylketone; nitriles such as acetonitrile, propionitrile, acrylonitrile; alcohols such as methanol, ethanol, is.

- propatool, butanol, ethylene glycol; esters such as ethyl acetate, amyl acetate; acid amides such as dimethylformamide, dimethylacetamide; sulfones, sulfoxides such as dimethylsulfoxide, sulfolane; and bases such as pyridine. I can do it.

Process a) can be carried out within a substantially wide temperature range. Generally, it can be carried out between about 0 and about 150<0>C, preferably between about 40 and about 80<0>C. Further, although it is desirable that the various reactions be carried out under normal pressure, they can also be operated under increased pressure or reduced pressure.

In carrying out production method a), for example, 1 mole of the compound of formula (II) is reacted with 1.0 mole to 3.0 times the mole of the compound of formula (III) in a solvent such as ethanol. The target compound can be obtained by

When carrying out the above manufacturing method b), as a suitable diluent,
Mention may be made of all inert solvents.

Examples of such diluents include water; aliphatic, cycloaliphatic and aromatic hydrocarbons (optionally chlorinated) such as hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene. , methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, 1,2-dichloroethane, chlorobenzene,
Dichlorobenzene; other ethers such as diethyl ether, methyl ethyl ether, and diis.

Propyl ether, dibutyl ether, propylene oxide, dioxane, tetrahydrofuran: ketones such as acetone, methyl ethyl ketone, methyl-1so-
Propyl ketone, methyl-1so-butyl ketone; Nitriles such as acetonitrile, propionitrile,
Acrylonitrile; alcohols such as methanol,
Ethanol, is.

-7' lovanol, butanol, ethylene glycol;
Esters such as ethyl acetate, amyl acetate; acid amides such as dimethylformamide, dimethylacetamide; sulfones, sulfoxides such as dimethylsulfoxide, sulfolane; and bases such as pyridine.

Process b) can be carried out within a substantially wide temperature range. Generally, it can be carried out between about 0 and about 150<0>C, preferably between about 40 and about 80<0>C. Further, although it is desirable that the various reactions be carried out under normal pressure, they can also be operated under increased pressure or reduced pressure.

In carrying out production method b), for example, 1 mole of the compound of formula (IV) is reacted with 1.0 mole to 1.1 times mole of the compound of formula (V) in a solvent such as ethanol. The target compound can be obtained by

When carrying out the above manufacturing method C), as a suitable diluent,
Mention may be made of all inert solvents.

Examples of such diluents include water; aliphatic, cycloaliphatic and aromatic hydrocarbons (optionally chlorinated) such as hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene. , methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, 1,2-dichloroethane, chlorobenzene,
Dichlorobenzene; Other ethers such as diethyl ether, methyl ethyl ether, di-iso-propyl ether, dibutyl ether, propylene oxide, dioxane, tetrahydrofuran; Ketones such as acetone, methyl ethyl ketone, methyl-1so-propyl ketone, methyl-1so- Butyl ketone; Nitriles such as acetonitrile, propionitrile, acrylonitrile; Alcohols such as methanol, ethanol, is.

-7' lovanol, butanol, ethylene glycol;
Esters such as ethyl acetate, amyl acetate; acid amides such as dimethylformamide, dimethylacetamide; sulfones, sulfoxides such as dimethylsulfoxide, sulfolane; and bases such as pyridine.

Preparation method C) is preferably carried out in the presence of an acid binder, such as alkali metal hydroxides, carbonates, bicarbonates, alcolades, etc. Tertiary amizos such as triethylamine, tributylamine, 1.1.4.4-tetramethylethylenediamine, N,N-dimethylaniline, N,
N-diethylaniline, pyridine, 4-dimethylaminopyrimidine (DMAP), 1,4-diazabicyclo(2
,2,2) octane (DABCO), 1,8-diazabicyclo(5,4,0)undec-7-ene (DBU)
can be mentioned.

Process C) can be carried out within a substantially wide temperature range. Generally, it can be carried out between about 0 and about 120°C, preferably between about 15 and about 80°C. Further, although it is desirable that the various reactions be carried out under normal pressure, they can also be operated under increased pressure or reduced pressure.

In carrying out production method C), for example, trifluoroacetic anhydride is added in an amount of 1.0 to 3.0 times the mole of the compound of formula (Ib) in a diluent such as methylene chloride,
The target compound can be obtained by reacting in the presence of 1.0 to 10 times the molar amount of pyridine.

The compound of formula (1) of the present invention exhibits a strong insecticidal action.

Therefore, they can be used as insecticides. 2N) The active compound of the present invention exhibits an accurate control effect against harmful insects without causing phytotoxicity to cultivated plants. Furthermore, the compounds of the present invention can be used to control a wide variety of pests, such as harmful sap-sucking insects, biting insects, and other plant-parasitic pests, storage pests, sanitary pests, etc., and can be applied to exterminate them.

Examples of such pests include the following. Insects include Coleoptera pests, such as Callosobruchus ch.
jnensis), brown weevil (Sitophilu
Trib s zeamais), Trib
olium castaneum), Epilachna vigintio
ctomaculata), Agriotes fuscicollis1, Anomala rufocuprea, Colorado beetle (Leptinotarsa d)
ecemlineata), Diaphroteica (Dja
brotica spp,),? '7/ Monochamus alternatus
, rice weevil (Lissorhoptrus)
oryzophilus), oyster beetle (Ly
ctus bruneus); Lepidoptera, such as Lymantria dispar, Malacosoma neustria
% Pieris rapae, Spodoptere Litura, Mamestra brassicae, Chil.

5uppressalis), Pyr moth (Pyr
austanbilalis),
Ephestia cautella), doxophyes orana, codling moth (Carpocapsa pomonella), capraya moth (Agrotisfucosa), honey moth (Galleria mellonella), diamondback moth (Plutella maculipennis),
leliothis () leliothis viresc
ens), Citrus leafminer moth (Phyllocnis)
tis citrella); Hemiptera, e.g. Nephotettix cinc
ticeps), brown planthopper (Nilaparva)
ta lugens), Pse.
ucfococcus colIlstocki), green scale insect (υnaspis yanonens)
Myzus pers”), Myzus pers
icae), apple aphid (Aphis pomi)
), cotton aphid (Aphis gossypii)
, Rhopalosiphu
mpseudobrassicas), Nasigunbai (
Stephanitisnashi), green stink bug (
Nezara spp, ), bed bugs (Cimex
Iectularius), Whitefly (Iectularius)
Trialeurodes vaporariorun
), Psylla spp,); Orthoptera insects, such as the German cockroach (Blatella germani);
ca), American cockroach (Periplaneta a)
Gryllotalpa), Gryllotalpa
africana), grasshopper (Locustamig)
ratoria m: gratoriodes):
Isopteran insects, such as Deucotermes 5pera
tus), Coptoterses f.
ormosanus); Diptera insects, such as Musca don+estica, Aedes aegypti, Hylemia platura, Culex pipienes,
Anopheles 5lnensis), Culextr i taen 1orhyn
chus), etc.

Examples of mites include Tetranychus telar.
ius), two-spotted spider mite (Tetranyhus urt)
icae), citrus spider mite (Panonychus c.
itri), citrus rust mite (Aculopspele)
kassi), dust mite (Tarsonemus s.
pp, ), etc.

Examples of nematodes include the sweet potato nematode (Meloidogyne).
incognita), pine nematode (Bur
, 5aphelenchus Ijgnicolus
Mamiya et Kiyohara), Aphelenchoidesbes
seyi), soybean cyst nematode (He tero
deraglycines), Negusare nematode (
Pratylenchus St) p, ) and the like.

Furthermore, in the pharmaceutical field of veterinary medicine, the novel compounds of the invention can be used to treat various harmful animal parasites (internal and external parasites).
, for example, are effective for use against insects and helminths. Examples of such animal parasites include the following pests.

Examples of insects include horse flies (Gastrophilus spp.),
Stomoxys spp, Trichodectes spp, Rhodnius spp, Cte
canis) and the like.

Examples of mites include Kazuki mites (Kanthodoros spp.),
Ixodespp, ), Bo
ophilus spp, ), etc.

In the present invention, substances having an insecticidal effect on earth including all of these substances may be referred to as insecticides.

The active compounds according to the invention can be put into customary pharmaceutical forms. And such forms include liquids, emulsions, and more!
! ! Clouding agents, aqueous phase agents, powders, foams, pastes, granules, aerosols, active compound infiltration - natural and synthetic products, microcapsules, seed coatings, preparations with combustion devices (e.g. combustion devices include fumigation) and fume cartridges, cans and coils), and ULV [cold mist]
cold m1st), warm mist (warm m
1st)].

These formulations can be manufactured by known methods. Such methods include, for example, combining the active compound with a developing agent, i.e.
This is carried out by mixing with liquid diluents; liquefied gas diluents; solid diluents or carriers, optionally surfactants, ie emulsifiers and/or dispersants and/or foam formers.

When using water as a developing agent, for example, organic solvents can also be used as co-solvents.

Liquid diluents or carriers generally include aromatic hydrocarbons (e.g. xylene, toluene, alkylnaphthalenes, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons [
(e.g., chlorohenzenes, ethylene chlorides, methylene chloride, etc.), aliphatic hydrocarbons (e.g., cyclohexane, etc., paraffins (e.g., mineral oil fractions, etc.)), alcohols (e.g., butanol, glycols, and their ethers and esters). ), ketones (eg acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, etc.), strongly polar solvents (eg dimethylformamide, dimethyl sulfoxide, etc.) and water.

The liquefied gas diluent or carrier is a gas at normal temperature and pressure, and examples thereof include butane, propane, nitrogen gas,
Mention may be made of aerosol propellants such as carbon dioxide and halogenated hydrocarbons.

Solid diluents include soil natural minerals (e.g. kaolin, clay, talc, chalk, quartz, acpal guide,
montmorillonite or diatomaceous earth), soil synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.).

Solid carriers for granules include crushed and fractionated rocks (e.g. calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic piles of inorganic and organic powders, and organic substances (e.g. sawdust, The fine grains of coconuts, corn cobs, tobacco stalks, etc.) can be mentioned.

Emulsifiers and/or foaming agents include nonionic and anionic emulsifiers [e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (e.g., alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, etc.). -rusulfonate, etc.)] and albumin hydrolysis products.

Examples of dispersants include lignin sulfide waste liquid,
and includes methylcellulose.

Sticking agents can also be used in the formulations (powders, granules, emulsions), such as carboxymethyl cellulose and natural and synthetic polymers such as gum arabic,
polyvinyl alcohol and polyvinyl acetate, etc.)
can be mentioned.

Coloring agents may also be used, including inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, ab dyes or metal phthalocyanine dyes, and also iron, Mention may be made of trace elements such as manganese, boron, copper, cobalt, molybdenum, their salts of zinc.

The formulations may generally contain from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight of said active ingredient.

The active compounds of the present invention, in their commercially useful formulations and the use forms prepared by those formulations, may be used in combination with other active compounds, such as insecticides, poison baits, fungicides, acaricides, It can also be present as a mixture with a nematocide, a fungicide, a growth regulator, or a herbicide.Here, the above-mentioned insecticides include, for example, organic phosphorus agents, carbamate agents, carboxylate agents, Examples include chlorinated hydrocarbon drugs and insecticidal substances produced by microorganisms.

Furthermore, the active compound of formula (1) of the present invention can also be present as a mixture with a synergist, and such formulations and usage forms can include those that are commercially useful. The synergist need not be active itself, but is a compound that amplifies the action of the active compound.

The content of active compounds of formula (1) according to the invention in commercially useful use forms can vary within wide limits.

The concentration for use of the active compounds of formula (I) according to the invention is, for example, from 0.0000001 to ioo% by weight, preferably from 0.00001 to 1% by weight.

The compound of formula (1) of the present invention can be used in a conventional manner depending on the usage form.

When used against sanitary pests and stored pests, the active compounds are distinguished by their good stability against alkalis on limestone materials, as well as their excellent residual activity in wood and soil. .

Next, the content of the present invention will be specifically explained with reference to Examples.
The present invention should not be limited to this only.

Production examples: Example 1 Example 2 l-(2-chloro-5-pyridylmethylamino)-1-
Methylthio-2-trifluoroacetylethylene (2,
A mixture of 0g), aqueous methylamine solution (30%, 2.0g), and ethanol (50ml) is stirred at 50°C for 2-3 hours.

Next, ethanol was distilled off under reduced pressure, and the residue was purified by column chromatography (eluent: ethanol/chloroform) to obtain 1-(2-chloro-5-pyridylmethylamino).
-1-Methylamino-2-trifluoroacetylethylene (1.5 g) was obtained.

no 1.5543 1-(2-chloro-5-pyridylmethyl)-2methyl-
3-Trifluoroacetylisothiourea (1,8g)
, methylamine aqueous solution (30%, 2.9 g), and ethanol (50 m/) are stirred at 50° C. for 2 to 3 hours.

Next, ethanol was distilled off under reduced pressure, and the residue was purified by column chromatography (eluent: ethanol/chloroform) to obtain 1-(2-chloro-5-pyridylmethylamino).
-1-Methyl-3-trifluoromethylacetylguanidine (1.2 g) is obtained.

mp, 109-113°C Example 3 0=C-CF:1 1-(2-chloro-5-pyridylmethylamino)-1-
Methylamino-2-trifluoroacetylethylene (1
, 5g), trifluoroacetic anhydride (4.2g) and pyridine (50mf) are stirred at 50°C for 8 hours.

Next, pyridine was distilled off under reduced pressure, and the residue was purified by column chromatography (eluent: ethanol/chloroform) to obtain 1-(2-chloro-5-pyridylmethylamino).
-1-Methylamino-2,2-bis(trifluoroacetyl)ethylene (0.5 g) is obtained.

m p , 103.5 to 104.5°C Compounds that can be produced in the same manner as in the above production example are shown in Example 1.2.
and the compounds prepared in 3 are shown in Table 1 below.

Production of intermediate: Reference example 1 1.1-bismethylthio-4,4,4-trifluoro-
A mixture of 1-buten-3-one (5.0 g), 2-chloro5-aminomethylpyridine (3.3 g) and tetrahydrofuran (100III1) is stirred at 50° C. for 3 hours.

Next, tetrahydrofuran was distilled off under reduced pressure, and 1-(2
-chloro-5-pyridylmethylamino)1-methylthio-2-trifluoroacetylethylene (7.1 g) is obtained.

mp, 101-105°C Reference Example 2 N-1-lifluoromethylcarbonyl-8,S-dimethyldithiocarbamate (7.6 g), 2-chloro-5-aminomethylpyridine (5.0 g) and tetrahydrofuran (100 mj) The mixture is stirred at 50° C. for 3 hours.

Next, tetrahydrofuran was distilled off under reduced pressure, and the residue was purified by column chromatography (eluent: ethanol/chloroform) to obtain 1-(2-chloro-5-pyridylmethyl)-2-methyl-3-trifluoroacetyl. Isothiourea (8.7 g) is obtained.

mp, 101-105°C Reference Example 3 2.2.2-) Lifluoroacetamide (50.0g)
, carbon disulfide (50,0 g) and (300 mj') at 0-5°C was added potassium hydroxide powder (85%, 6
3.0g) little by little. After stirring for 1 hour, dimethyl sulfuric acid (10.6 g) was added dropwise while maintaining the temperature, and the mixture was further stirred for 1 hour. Pour the reaction mixture into water! After drying over anhydrous sodium sulfate, the solvent was distilled off to obtain N-trifluoromethylcarbonyl-8,S-dimethyldithiocarbamate (67.0 g).

Reddish brown oil I R(νC=0.1660an-')'HNMR(C
DC13, δ, TMS) 2.58 (s, 6H) Biological test example: Comparison E-1 (compound conceptually included in EA-A 302389)
Comparison E-2 Example 4 Preparation of test sample solution against organophosphorus resistant black leafhopper Solvent: Kijirol 3 parts by weight Emulsifying side: Polyoxyethylene alkyl phenyl ether 1 part by weight Active to prepare a suitable active compound formulation One part by weight of the compound was mixed with the amount of solvent containing the amount of emulsifier, and the mixture was diluted with water to the desired concentration.

Test method: A water diluted solution of the active compound at a predetermined concentration prepared as described above was sprayed on rice plants with a plant height of 10 (: 11) planted in pots with a diameter of 12 cm. A wire mesh with a diameter of 7 cm and a height of 14 cm was placed over the wire mesh, and 30 female adult leafhoppers of a strain that is resistant to organic phosphorus agents were released into the wire mesh, placed in a thermostatic chamber, and after 4 days, the number of dead and alive was counted to calculate the insect kill rate.

The results are shown in Table 2.

(Compounds conceptually covered by EP-A 302389)
Table 2 Compound concentration Active ingredient concentration (ppm) 2
1000 00 0 1.6 25 1000 00 0 Comparison E-11000 00 Comparison E-21000 00 0 Insect killing rate % 00 00 00 00 00 00 00 00 0 00 0 0 10a+1 per bot of water diluted solution of specified concentration! Spread. After the sprayed chemical solution has dried, cover it with a wire mesh with a diameter of 7 cm and a height of 14 am, and release 30 female adult brown planthoppers of a strain that is resistant to organic phosphorus agents into the mesh, place it in a constant temperature room, and check the number of dead and alive after 4 days. The insect killing rate was calculated.

In the same manner as above, the insecticidal rate against the brown-bottomed planthopper and the organophosphate-resistant brown planthopper was calculated. The results are shown in Table 3.

Example 5 Test method for planthoppers: Rice plants with a plant height of about 10 aa planted in pots with a diameter of 120 were injected with the procedure amendment (
Spontaneous) L, Indication of the case, Patent Application No. 2-11947 2, Title of the invention: Insecticidal trifluoroacetyl derivative 3, Person making the amendment Relationship with the case

Claims (1)

[Claims] 1) Formula ▲ Numerical formula, chemical formula, table, etc. ▼ In the formula, Z represents a 2-chloro-5-thiazolyl group or a 2-chloro-5-pyridyl group, and R^1 and R ^2 represents a hydrogen atom or a methyl group, R^3 represents an amino group, methylamino group, or dimethylamino group, and Y represents CH, N, or ▲a mathematical formula, chemical formula, table, etc. ▼
shows. A compound represented by 2) Z represents a 2-chloro-5-pyridyl group, and R^1
represents a hydrogen atom, R^2 represents a hydrogen atom or a methyl group, R^3 represents a methylamino group, and Y represents a CH
, N or ▲There are mathematical formulas, chemical formulas, tables, etc. ▼ The compound according to claim 1). 3) 1-(2-chloro-5-pyridylmethylamino)-
1-Methylamino-2-trifluoroacetylethylene, 1-methylamino-1-{N-methyl-N-(2-chloro-5-pyridylmethyl)amino}-2-trifluoroacetylene, 1-(2- Chloro-5-pyridylmethylamino)-1-
Methylamino-2-trifluoroacetylguanidine and 1-(2-chloro-5-pyridylmethylamino)-1-
Methylamino-2,2-bis(trifluoroacetyl)
The compound according to claim 1) or 2), selected from ethylene. 4) Formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, Z represents a 2-chloro-5-thiazolyl group or a 2-chloro-5-pyridyl group, and R^1 and R^2 are each , represents a hydrogen atom or a methyl group, R^3 represents an amino group, methylamino group, or dimethylamino group, and Y represents CH, N, or ▲Mathematical formula, chemical formula, table, etc.▼
shows. An insecticide containing the compound represented by as an active ingredient.